Following is an outline of one of the first syntheses of the antidepressant fluoxetine (Prozac). „NMe, Но. NMe, NMe, A B C D. OEt NMeg OE F,C Me CH,ONa FC F&C E F ÇOOH Me `Me F.C F,C An N-substituted Fluoxetine carbamic acid

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter3: Organic Compounds: Alkanes And Their Stereochemistry
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Problem 50AP: Formaldehyde, H2C=O, is known to all biologists because of its usefulness as a tissue preservative....
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Propose a reagent or reagents to bring about the conversion of F to fluoxetine. Note that the bracketed intermediate formed in this step is an N-substituted carbamic acid. Such compounds are unstable and break down to carbon dioxide and an amine.

Following is an outline of one of the first syntheses of the antidepressant fluoxetine
(Prozac).
„NMe,
Но.
NMe,
NMe,
A
B
C
D.
OEt
NMeg OE
F,C
Me
CH,ONa
FC
F&C
E
F
ÇOOH
Me
`Me
F.C
F,C
An N-substituted
Fluoxetine
carbamic acid
Transcribed Image Text:Following is an outline of one of the first syntheses of the antidepressant fluoxetine (Prozac). „NMe, Но. NMe, NMe, A B C D. OEt NMeg OE F,C Me CH,ONa FC F&C E F ÇOOH Me `Me F.C F,C An N-substituted Fluoxetine carbamic acid
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